The focus of this research is the rational development of nonracemic sulfur-nitrogen reagents, including N-sulfonyloxaziridines, sulfenimines and primary sulfonamides,for efficient preparation of enantiomerically pure compounds. Not only will this provide the enantioselective synthesis of previously inaccessible compounds but also a better understanding of the molecular recognition involved with these reagents. Specifically, new N-sulfonyloxaziridine oxidants will be used to prepare enantiopure sulfoxides, selenoxides, and sulfinimines. New reagents derived from optically active primary sulfonamides, N-sulfinylsulfonamides, N-chloro-N-sodiosulfonamides, and (N-sulfonylimino)phenyliodinanes will be evaluated in the asymmetric synthesis of aziridines and beta-amino alcohols. Site-specific fluorination will be explored with new chiral N-fluorosulfonimides. %%% With this Renewal award, the Synthetic Organic Program is supporting the research of Dr. Franklin A. Davis of the Department of Chemistry at Drexel University. Professor Davis will focus his work on the rational development of nonracemic sulfur-nitrogen reagents for efficient preparation of enantiomerically pure compounds. He also will explore the site-specific fluorination of compounds using new chiral reagents.
